Cuba tours & tailor-made trips

Plan your dream trip to Cuba with a local expert

See a different side to Cuba on a trip built just for you, by someone who lives there.

Custom itinerary planningHandpicked local experts
Complete peace of mindASTA membership, financial protection & 24/7 local support
A fairer way to travelBenefiting local communities
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Let Cuba’s rhythm take the lead, from salsa in Havana’s plazas to sunrise over the tobacco fields of the Viñales Valley.

Cuba is a Caribbean destination that knows how to live out loud: think pastel facades in Old Havana, the soulful sound of a trumpet drifting across Trinidad’s cobbled plazas, and strong, sweet cafecito on a sunny porch.

To let Cuba reveal itself to you authentically, plan your trip with someone who calls it home. Our trusted local experts will design a trip around you, opening doors to family-run casas and local haunts.

Your Cuba adventure awaits

Best time to visit

Best for sunshine and exploring: November to April
Carnival season: Santiago de Cuba comes alive with music and color in July

Destination highlights

Cuba truly unfolds beyond Havana’s grand boulevards. Cycle past tobacco farms and limestone mogotes in the Viñales Valley, wander the colonial streets of UNESCO-listed Trinidad, or snorkel the clear waters of the Bay of Pigs. Farther east, Santiago de Cuba pulses with Afro-Caribbean music while laid-back Baracoa offers cacao farms and rainforest-cloaked rivers far from the crowds.

Price overview

US $1,000 - $1,500+

All of our tailor-made trips can be 100% customized to your style—from budget stays to higher-end escapes. Prices are per person, based on a 7-day trip.

Best time to visit

How it works

How would you like to plan your trip?

Build a trip from scratch with a local Cuba expert, or pick a curated itinerary as your starting point and customize it until it's yours.

  • Share your preferencesTravel dates, budget, experiences and more
  • Connect with your local expertReceive your first itinerary within 48 hours
  • Refine your trip togetherFull flexibility and a hassle-free, personal service
  • Book with confidence24/7 support, secure payment, ASTA protected

Free to plan. No commitment until you book

Trip ideas

Recommended trips to Cuba

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Meet your local experts

Your trip, planned by someone who actually lives there

Our local experts aren’t travel agents working from a brochure. They’re people who live locally and know the destination like the back of their hand. Alongside them, you’ll craft an authentic and immersive trip, filled with intimate knowledge and passion for the place they call home.

Start planning your trip
  • Luis

    I’ll help you plan a trip that’s perfect for you, filled with unforgettable experiences that reveal the essence of my home country…

  • Francisco

    Plan for extra time in Viñales to explore tobacco plantations, taste coffee, learn about traditional cigar-making, or ride on horseback through the countryside.

  • Francisco

    By working with TravelLocal, we've generated more sustainable tourism which directly benefits small businesses and residents, and invested in training and capacity-building for local guides.

Traveler stories

What our travelers are saying

Dilipitated building in Vedado neighborhood of Havana, Cuba
The assistance and promptness of response of TravelLocal staff and the friendliness of Cuban people. We would recommend TravelLocal to our friends considering travel to Cuba.
William Robert McPheeTraveled in February 2026
Traveler Coleen Swanson in Cuba
My husband and I had an unforgettable experience in so many ways. Our travel coordinator, Francisco, was the best that we have ever encountered. TravelLocal's contact people made sure that we were well taken care of and were present every step of the way.
Coleen SwansonTraveled in February 2026
Horseback riding in Vinales, Cuba, one of the best winter vacation destinations
The country is so beautiful with such welcoming people. We were able to make the most of this because of the way this trip was organised, coordinated and supported while we were in Cuba. It was based on our individual interests.
Sally ChaplinTraveled in January 2026
Dilipitated building in Vedado neighborhood of Havana, CubaTraveler Coleen Swanson in CubaHorseback riding in Vinales, Cuba, one of the best winter vacation destinations+78k

78,000+ travelers have had a more authentic, tailor-made vacation

Places & highlights

Learn more about Cuba

Take the family to Cuba

Take a look at our guide to Cuba for families: with a bit of planning, this Caribbean country is a top pick if you have the kids in tow.

Good to know

Frequently asked questions about Cuba

Straße in Trinidad, Kuba

  • Yes, but not as tourists. Every trip must fit one of 12 categories set by the US Treasury, and you will find these on the US embassy’s website.

  • You’ll need a passport valid for at least six months beyond your arrival date, proof of travel insurance with medical coverage, and a return or onward ticket. You will also require a visa that covers one of the 12 visa categories. Check travel requirements carefully before planning your trip.

  • The US State Department rates Cuba at Level 2, Exercise Increased Caution, because of rising crime and unreliable electricity. Petty theft is the most common issue, so keep valuables close. Power outages last for hours each day, so plan for blackouts by packing a flashlight and a power bank, and avoid protests.

  • The Cuban Central Bank has announced that international cards such as Visa and Mastercard are no longer accepted. Instead, use cash and Cuban prepaid cards. You won’t be able to withdraw cash through ATMs with an international card either, so bring enough cash for the whole trip.

  • November through April is the dry season when you can expect sunny days, lower humidity, and comfortable temperatures, making it the most popular time to go. May to October is hotter and wetter, and hurricane season runs June through November, peaking from August to October. Shoulder months often bring fewer crowds and better value for travelers.

  • Casas particulares, Cuba’s family-run guesthouses, are the best way to experience everyday life. You will be able to enjoy home-cooked breakfasts, and your hosts will be able to supply you with local tips and advice. Staying in one also counts as a qualifying activity for Americans traveling under “support for the Cuban people.” Americans may not stay at hotels on the State Department’s Cuba Prohibited Accommodations List.

Next steps

Ready to start planning your Cuba trip?

Tell us what you’re looking for and we’ll match you with a local expert who knows the destination inside and out. It’s free to get a quote.

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